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Head of Upper School

Job in San Diego, San Diego County, California, 92189, USA
Listing for: DRG Talent
Full Time position
Listed on 2026-01-27
Job specializations:
  • Education / Teaching
    High School, School Principal, Education Administration, Teacher Assistant/ Paraprofessional
Job Description & How to Apply Below

Background

La Jolla Country Day School is pleased to work with DRG to conduct this search. Read the full Opportunity Statement.

Founded in 1926, La Jolla Country Day School (LJCDS) is San Diego’s only independent, coeducational school serving students from age three through grade twelve on a single campus. This PreK–12 continuum is a defining strength, allowing students to grow together in a community where leadership, empathy, and self-awareness are learned alongside rigorous academics. LJCDS is guided by a mission to prepare individuals for a lifetime of intellectual exploration, personal growth, and social responsibility and by a core commitment to dignity: the belief that every person has inherent worth and value.

Today, LJCDS serves an engaged and high-achieving student body drawn from across the region. The school enrolls approximately 1,169 students, including up to 500 in the Upper School, and is supported by a deeply committed faculty with an average tenure of ten years. With strong resources and an ambitious program that integrates academics, athletics, arts, service, and global engagement, LJCDS offers students an education that is both demanding and deeply human.

A signature initiative shaping the school’s future is The Hub for Human Impact, a new 20,000 square-foot human-centered learning commons opening in fall 2026. Designed to bring students together across disciplines and age groups, The Hub will support design thinking, innovation, entrepreneurship, global collaboration, and experiential learning. It reflects LJCDS’s commitment to preparing students not simply for college, but for leadership and impact in an increasingly complex world.

Opportunities

and Challenges

The Head of Upper School role presents a compelling leadership opportunity that blends continuity with change. The division is grounded in a strong academic culture, committed faculty, and capable, engaged students while also navigating strategic, cultural, and structural shifts that call for clarity, steadiness, and thoughtful execution.

A central opportunity lies in advancing the Upper School’s evolving academic vision. The advanced studies framework reflects a commitment to deeper learning and long-term student success. The next Head of Upper School will steward this work and articulate its value clearly to students, families, and faculty.

Another significant opportunity is strengthening leadership structures and accountability. With an administrative team in transition and department chairs assuming greater responsibility, the incoming Head will have the ability to clarify roles, build a healthy leadership model, and establish consistent expectations that support both growth and excellence.

Culturally, the role offers the opportunity to center decision-making on students while building trust among adults. Balancing empathy with clarity and warmth with accountability will be essential.

The role also includes close partnership with a highly engaged parent community. College counseling in particular is a visible and important area of focus, requiring thoughtful communication and alignment between academic pathways and postsecondary outcomes. Strengthening confidence in the Upper School experience, especially in collaboration with Middle School leadership, will be key to retention and enrollment stability.

Finally, the Head of Upper School will play a central role in integrating The Hub for Human Impact into the academic and co-curricular life of the Upper School, ensuring that its promise translates into meaningful student learning and community engagement.

The Position

The Head of Upper School is the senior leader responsible for the academic, cultural, and operational vitality of grades 9 through 12. Reporting to the Head of School and working closely with the Associate Head of School and fellow division leaders, the Head provides vision, leadership, and daily oversight for a complex and engaged Upper School community.

Responsibilities
  • Leading the overall Upper School student experience
    ; setting the tone for a culture rooted in dignity, belonging, and high expectations; and ensuring that students feel known, supported,…
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